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Set Windows Server 2008 R2 SMTP for Opportunistic TLS

I use a Windows 2008 R2 server for sending (relaying) outbound emails to clients. Many of these clients are now requiring TLS connections to send them email. To date I have set up a an SMTP "Remote Domain" and forced TLS to that domain. Keeping up with the list of domains is becoming a daunting task. A. Windows SMTP doesn't have an easy way to script the addition of remote domains, and B. there is no way to import or export the domains.

To remove all this manual work we would like to set up opportunistic TLS on the server so any receiving SMTP server requesting TLS, my server will connect using TLS. Is this at all possible to setup in Windows Server 2008 R2?

    • I don't know the answer to your question, but I'd like to point out that the SMTP Server role in 2008 R2 and later is deprecated and only available for backwards compatibility. You might want to look elsewhere for a more long-term solution.

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